title: In silico optimization of merocyanine-spiropyran compounds as second-order nonlinear optical molecular switches.
abstract: Time-dependent Hartree-Fock and Møller-Plesset second-order calculations have been used to unravel the relationships between structure and first hyperpolarizability in spiropyran/merocyanine couples and therefore to design efficient second-order nonlinear optical switching compounds. Large first hyperpolarizabilities for the merocyanine form as well as large contrasts of first hyperpolarizability have been obtained when, on the same species, (i) substituents at R(1) and R(2) positions on the phenolate ring of the merocyanine form are strong acceptor and donor substituents, respectively, (ii) the ethylenic bridge is substituted by donor groups, (iii) the other aromatic part of the system is benzimidazolo rather than indolino or benzothiazolo, and (iv) strong donor substituents are placed on the benzimidazolo moiety.
authors.affiliation: Laboratoire de Chimie Théorique Appliquée, Facultés Universitaires Notre-Dame de la Paix, rue de Bruxelles 61, Namur, Belgium.
authors.forename: Aurélie
authors.initials: A
authors.lastname: Plaquet
authors.forename: Maxime
authors.initials: M
authors.lastname: Guillaume
authors.forename: Benoît
authors.initials: B
authors.lastname: Champagne
authors.forename: Frédéric
authors.initials: F
authors.lastname: Castet
authors.forename: Laurent
authors.initials: L
authors.lastname: Ducasse
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Pozzo
authors.forename: Vincent
authors.initials: V
authors.lastname: Rodriguez
mesh_terms: D001562:Benzimidazoles / Q000737:chemistry; D001578:Benzopyrans / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007700:Kinetics; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D017711:Nonlinear Dynamics; D011744:Pyrimidinones / Q000737:chemistry*; D011789:Quantum Theory; D013329:Structure-Activity Relationship
chemical_list: D001562:Benzimidazoles; D001578:Benzopyrans; D005030:Ethylenes; D007211:Indoles; D009574:Nitro Compounds; D011744:Pyrimidinones; C088184:spiropyran; C003954:merocyanine dye; C036216:ethylene